Nucleophilic and Electrophilic Double Aroylation of Chalcones with Benzils Promoted by the Dimsyl Anion as a Route to All Carbon Tetrasubstituted Olefins

…, G Fantin, M Fogagnolo, PP Giovannini…

Index: Bortolini, Olga; Fantin, Giancarlo; Fogagnolo, Marco; Giovannini, Pier Paolo; Massi, Alessandro; Pacifico, Salvatore Organic and Biomolecular Chemistry, 2011 , vol. 9, # 24 p. 8437 - 8444

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Citation Number: 10

Abstract

Dimsyl anion promoted the polarity reversal of benzils in a Stetter-like reaction with chalcones to give 2-benzoyl-1, 4-diones (double aroylation products), which, in turn, were converted into the corresponding tetrasubstituted olefins via aerobic oxidative dehydrogenation catalyzed by Cu (OAc) 2.